


Dean Winchester Is So Bi (Bisexual Pride Day)

by Shtwriter_yup_datsme



Series: Pride Month Oneshots! 🌈 [3]
Category: Supernatural
Genre: Bisexual Dean Winchester, Coming Out, Fluff and Smut, Kissing, LGBTQ Themes, M/M, Past Relationship(s), Smut, Supportive Sibling Sam Winchester
Language: English
Status: Completed
Published: 2020-06-03
Updated: 2020-06-03
Packaged: 2021-03-04 07:07:25
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,532
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24519694
Author URL: https://archiveofourown.org/users/Shtwriter_yup_datsme/pseuds/Shtwriter_yup_datsme
Summary: Dean sees a blast from the past
Relationships: Castiel/Dean Winchester, Leo Webb/Dean Winchester
Series: Pride Month Oneshots! 🌈 [3]
Series URL: https://archiveofourown.org/series/1768747
Comments: 8
Kudos: 68





	Dean Winchester Is So Bi (Bisexual Pride Day)

His first kiss is with a girl..Amber something, Dean was 14 he thought she was cute, he liked her and she had a brother maybe 16?

Dean thought he was _also_ cute, it was so confusing- especially when he started to see more guys like he did girls as he got older

It'd been forever.. _years-_ it's not that he's ashamed he just doesn't _talk_ about it

Though he called it experimenting at the time, he messed around a lot but of course kept it under wraps, he never really got involved with feelings but then he met Cassie and he fell in love..but..it hadn't worked out

And then there was Leo- for guy who had so many walls he sure fell easy, but after Lisa he was done..or so he thought because apparently blue eyed sex haired angels make his heart skip a beat

But he didn't go for it- he knew that he _could_ but he didn't..

_You can bury the past, but after a while it catches up with you- and you can't do anything but man up and face the music_

"I'm gonna go to the bathroom" Sam said and stood walking off; they were on a case and decided to head off to a bar that one of the victims frequented to go over their facts

Dean sighed and looked around the bar, there was a good variety of people in it, after a few seconds he averted his eyes to the drinks menu

Dean smiled softly staring at the drinks menu, every special drink was lgbt+ themed, he wasn't completely sure but it must've been pride month

He shrugged and happily ordered a 'Bisexual blast', giving a playful wink to the female bartender, he sighed and waited for Sam to get back from the bathroom

When his drink came it surprisingly tasted pretty fucking great, it was ombré mimicking the colors of the bisexual flag- not to mention the alcohol that was in it

"What's that?" Sam asked when he came back sitting down, Dean shrugged "Pride month drink- bisexual blast, tastes pretty good"

Sam eyed his brother, "Huh, guess I'll get one to" He decided not to mention how comfortable Dean was with his choice of drink

As Dean chugged down some more of his colorful drink his eyes wandered again and he almost passed out when he saw who he thought was a literal ghost

"Leo frickin Webb?"

The man turned around and his eyes were wide just like Dean's, "Dean Winchester?" He said in disbelief, "Oh my god- you..you're alive" Dean stuttered

Leo nodded just as shocked "So are you.." Sam blinked watching the two "Um, hi?"

Dean shook his head, he had forgot that his brother was there for a moment "Yeah- um Lee this is Sam my brother" Leo frowned "Sammy?" Sam rolled his eyes "It's just Sam" He said slightly annoyed "So I take it you two know each other?"

Dean nodded "Yeah we hunted together with dad when you were in college, god..it's been what?- 10 years?" Leo shrugged "More or less" He said "What are you even doing here?" Dean asked curiously

Leo looked around "I own this place" He exclaimed, Dean frowned "You _own_ this place?" It kind of made sense- especially the drinks, Leo was always comfortable with his sexuality and wasn't afraid to show it

But what was more surprising was that he and Leo had the dream of running a bar together when they were younger..but Dean never thought that Leo would actually make that dream a reality

Leo nodded happily "Yup- all mine" He huffed "So lemme guess you're on a case?"

Sam nodded "Yeah, vengeful sprit looks like" They chatted some more about the case and Leo joined them for drinks even toasting to the late John Winchester (but honestly the guy didn't die soon enough)

~🌈~

Sam got separate bedrooms for him and Dean because he had seen how Dean eyed the bartender chick from the bar and he really didn't want to be apart of _that_

Dean was in his room, he'd just gotten out of the shower when a knock sounded at the door, he frowned slightly- Sam wouldn't knock so he grabbed his gun and advanced for the door slowly opening it and praying that the towel around his waist wouldn't fall

When he opened the door he had his gun pointed at the person who had knocked so fast they put their hands up "Lee?"

"Jeez- I forgot how much of a _hunter_ you are" He put his hands down "You gonna let me me in?"

Dean lowered his weapon and Leo entered the room looking around "What are you doing here?" Dean asked sort of redundantly already knowing why Leo was there, probably a booty call

Leo shrugged "Couldn't stop thinking about you" He answered nonchalantly "Thought seeing you would get it out of my system" He looked at Dean's half naked state "I was obviously wrong"

Dean looked down and felt his cheeks redden, he had forgorten that he was only in a towel, Leo sat down on the edge of the bed, gently chewing his lip "I don't know..I guess old habits die hard" He sighed "..Sam doesn't know about you does he?" He asked and Dean gave a heavy sigh putting his gun down "..No"

Leo sighed "Dean seriously?" Dean shrugged lightly "I'm pretty sure he knows.."

Leo raised his brows "You're 'pretty sure'?"

Dean grabbed another towel "Sam's not stupid- I just don't want to have to go through the whole 'coming out thing'" He dried off his hair "I'm not ashamed I just don't see why it's anyone's business who I fuck"

"But he's your brother Dean, you have to tell him you've been in the closet for over 10 years because of your father" Leo said "And you weren't exactly subtle with that drink at the bar, you _want_ him to know"

" _Ugh_ \- are you ever not the voice of reason?" Dean rolled his eyes "Fine- I'll tell him, remind me how we lasted so long?"

Leo smirked, he stood and grabbed Dean kissing him roughly, Dean's hands went into Leo's hair, the kiss was hard and passionate, Leo moaned into the kiss, causing Dean to want more, he licked at the entrance of the other hunter's mouth, he opened for Dean instantly and their tongues were intertwined

Leo's hands were pulling at Dean's hips, dragging their bodies together, their bodies touched from top to bottom, and Dean could feel his own erection against the towel hitting Leo's

Leo sucked his neck trying not to grin triumphantly at how he made Dean moan, his hand tugged at Dean's towel and it fell to the floor "..That's why"

~🌈~

The next morning Sam woke up early he spent about an hour researching about their case and when he'd found something he left his room and made his way to Dean's to inform his brother on what he had found

He didn't even think to knock before opening the door, he saw Dean on top of someone as they kissed, covers pulled up over them- he'd thought that Dean brought a girl over but he soon realised that it was Leo and the man had noticed him too

"..Uh Dean?" Leo said trying to inform his lover of Sam's appearance but Dean just kissed him again "What is it Lee?"

Leo whispered "..Your brother is here" Dean frowned and looked behind himself to find Sam awkwardly standing at the door, he rolled his eyes "Are you a professional cock block or something Sammy?"

Leo blinked in surprise at how cool Dean was being, "I just uh I found something- a-about the uh..case" Sam stuttered and Dean groaned seemingly bored with the whole situation he lazily rolled of Leo and onto his side "..That's nice Sammy- just gimme five more minutes"

Leo rolled his eyes _for_ Sam, "We'll be out in 10" Sam nodded as he started to leave the room he was stopped by a yell from Dean "Make that 20!"

~🌈~

"I mean't what I said, I'm gonna tell him" Dean said, just before they were leaving to meet up with Sam

Leo smiled at him and he shrugged "I know, I trust you" Dean frowned watching Leo leave the room he scoffed and followed after him

When they got to Sam's room luckily Sam didn't make a big deal out of what he had seen and they talked about the case

He'd been professional, until him and Dean were in the car alone together, "So..you and Leo huh?- is that new?..are you?..I didn't want to say anything at the bar" Sam stumbled over his words a little

"I'm bisexual- swing both ways, always have" Dean said easily staring out of the window, laying all cards on the table, Sam frowned "Always?- how long have you known?"

Dean shrugged finally looking away from the window "I guess since I was 12..Daphne may have been hot but Fred.. _god_ _I_ _loved that sexy_ _ascot_ " He said and Sam grimaced at how his brother bit his lip probably thinking of the cartoon character

But then realised something "You can't possibly think that I wouldn't be okay with you being bi?-" He seemed offended "I love you Dean- you're my big brother, I don't care who you like you're still gonna be the same jerk you've always been"

Dean sniffed, "Yeah..thanks" He didn't really show how much Sam's approval mean't to him but Sam knew that it was all the emotion he would get

Sam took a moment "..What about Leo?"

Dean didn't really want to talk about his past with Lee- because it was theirs but he did want to give Sam something after all he wasn't freaking out "..We were just friends at the start but then I fell for his..well everything- it wasn't so much romantic as it was just us having fun" He explained "It wasn't easy especially keeping it from dad"

"..So what happened why did you guys spilt?"

Dean shurgged "We had fun, we knew it wasn't.. _serious_ " He forced out the words

Sam couldn't pass up the chance  
"Is that what you're doing with Cas?" Dean shook his head as warning "Don't go there..just don't"

"What?- if you don't care that he's a guy then what are you scared of?"

Dean pulled over as they got to their destination "I love him okay?- what if I tell him and it doesn't work out..I..I can deal with us being just friends"

"What about him Dean?-what about Cas?- how _he_ feels?"

Dean sighed calming down; he knew that Cas had feelings for him, he'd _always_ known he just played dumb but he wasn't blind "..I don't know about- Cas"

"..Did you love Leo?- _do_ you love him?"

Dean stared out the window "Sam don't ask me that"

"Cassie, Lisa..you loved them so _did you love Leo-_ it's a simple question Dean"

Dean opened the car door "Yeah well I ain't giving a simple answer" He was done with the conversation leaving Sam to wonder why the hell his brother was so emotionally constipated

~🌈~

_"Night Mr Winchester!" Leo yelled as the door fell closed, he turned back to Dean and smiled_

_Dean rolled his eyes "You know you don't have to call him that, he adores you" He said trying not to sound jealous that his father cared for some.. -random stranger more than him_

_Leo blinked "I was just being polite"_

_Dean scoffed "Yeah,"_

_"You gotta problem with me Winchester?- or is this your way of flirting with me?" Leo teased and Dean grimaced "_ _What-no_ _I'm not flirting with you" Maybe he thought that Leo was.. aesthetically pleasing but he didn't like him like that!_

_Leo paused "Right..w_ _ell_ _I'm gonna go to bed" He drunkenly tried to stand but ended up falling into Dean's lap on the floor_

_"Whoa-" He caught him in his lap and Leo lifted his head "Hi" They were so close if either moved their lips would meet_

_Dean swallowed nervously- why was he blushing??? "Um, sorry" He mumbled and Leo smirked and brought a hand to Dean's cheek "You really are adorable Winchester" He teased and leaned in pressing his lips to Dean's_

_Dean hesitated before he finally kissed back, he could taste the copious amounts of alcohol that Leo had drank on his tounge, humming softly he let Leo take control, the other man's hands were everywhere he wasted zero time in exploring Dean's body with his hands_

_It'd been a while since he'd been with a guy, 2 years to be exact, last time his dad caught him..it wasn't great, "Leo wait" He put a hand on Leo's chest as he started to pull up Dean's shirt "M-My dad..he can't- can't know"_

_Leo shook his head "He doesn't have to know babe, promise" Dean shivered at the pet name, "Now..we doing this or what?"_

_Dean rolled his eyes "Shut up and kiss me" Leo grinned, he kissed Dean's neck "I knew I wanted you the second I saw you"_

_Dean moaned lowly "Yeah?" He asked "Then take me" Leo growled playfully, excepting Dean's challenge, he picked Dean up off the floor and they made it to the bed_

_He layed Dean down and they wrestled, rolling around the cheap motel bed lips staying attached_

_Eventually they settled and Leo ended up on top, pinning Dean down "Clothes?"_

_"Clothes" Dean agreed and they temporarily parted discarding of all their clothes except for boxers, Leo chuckled "Really Dean-O Batman boxers?"_

_Dean scoffed "Don't judge me okay?" Leo smiled lifting his hands defensively "I'm not, I promise"_

_He wrapped his hands around Dean and flipped him over onto his stomach, he pressed himself into Dean grinding his erection against Dean's ass_

_He kissed down from Dean's neck down his back and to the waist band of his batman boxers, Dean sucked in a breath as his shorts were tugged down and pulled off of him_

_"Lee..no lube"_

_Leo shook his head "No problem" He spread Dean's cheeks and licked his hole, "Ah!"_

_He slipped a finger into Dean's tight entrance and Dean tensed around him "Relax" Leo whispered and Dean nodded relaxing around Leo's finger_

_He soon added another, opening up Dean more "Fuck you're tight, when's the last time you've been fucked?"_

_"Uh..I'm not-"_

_"Not what?- into guys too?" Leo scoffed "I'm not stupid Dean- not to mention I'm knuckles deep in your ass so.."_

_"-It's been a while, didn't want my dad to find out.. again" Dean said "Ah!-fuck!" Dean moaned when Leo hit his prostate_

_Leo smirked, he dragged his fingers out and palmed himself "Are you ready?"_

_Dean nodded "Yeah"_

_Leo pushed inside of Dean and the man let out a grunt, Leo gripped his waist tightly as he completely bottomed out in Dean's ass "Fuck baby, you're tight" He squeezed Dean's soft ass and Dean groaned "Move lee"_

_"Gimme a few, if I move I swear to god I'll come" He gave it a few seconds before he finally moved, he sped up his pace and Dean whimpered_

_It hurt, but the alcohol made it bearable and Dean can't be bothered when he just feels so fucking full- he can't breathe, and he doesn't think Leo can either not with the way the guy's fingernails were digging into his hips to keep himself still_

_In that moment, in the complete silence, Dean knows he has been completely ruined_ _"Mmph Lee," Dean bit the pillow, "Harder" Leo groaned and complied with Dean's request, going reasonably faster_

_Dean never realised how much he had missed this, having sex with another guy, girls are great and all but he always has to take the lead- he can't help it if he likes to be thrown around a bit or taken care of, it's not like he get's a lot of love from his current lifestyle_

_Leo on the other hand did what he wanted with whomever he wanted,_ _which the younger boy envied_

_Dean really tried to keep in his moans to keep his dad from hearing them through the crappy motel walls but with the way Leo was abusing his spot it was extremely hard_

_Leo moaned, he bent down and kissed Dean on the back of his neck "De..wanna- wanna fuck your mouth_

_God if that didn't just feed Dean's erection "Fuck yes" He consented and Lee pulled out, Dean turned around and got onto his knees before Leo's pre cum leaking cock_

_Leo nudged Dean's mouth open with his length and Dean took as much as he could_ _, L_ _eo started to gently fuck his mouth, chasing a release, Dean's hand fell to his own cock and he stroked it fast_

_Lee was surprised Dean was barley even choking and how much he could take was a lot, he held on to Dean's hair tightly and got rougher, just a little faster and drool fell from Dean's lips_

_Dean stared up at him as he jerked himself off and Leo soon came and flooded Dean's mouth with his cum, Dean swallowed but was still palming his own cock, Leo pulled himself from Dean's spent mouth and fell onto a pillow_

_Dean fell back as well and his hand movements sped, "Fuck-fuck-fuck!" He gave a long moan as he came all over his thighs, he slowed down when he began to twitch because of sensitivity_

_After a few seconds of breathless panting both boys began to laugh hysterically "Oh, damn..that was the best I've had in years" Leo announced and Dean nodded "Same here"_

_Leo sighed "..Hey what did you mean when you said you didn't want your dad to find out again?" Leo asked softly, Dean tensed up a little "..Nothing"_

_"You can trust me Dean" Leo assured "After all we just had some awesome sex"_

_Dean smiled a bit, deciding to tell Leo "..I was eighteen, my dad caught me with a..boyfriend- after he would barley even look at me" He chewed his lip "..Scared me so bad I swore off guys"_

_"I know it's not wrong but..it doesn't stop me from hating myself a little more everyday"_

_"Hey," Leo said gently "you shouldn't hate yourself for something you know you can't help, because I for one think you're awesome"_

_Dean smiled to himself "..Sounds like something my little brother would say, he's a total girl"_

_Leo laughed "Oh, fuck you_ _Winchester" Dean grinned "You already did" Leo grinned back "_ _Just please tell me there's gonna be more of this" He gestured between them_

_"Definitely" Dean said confidently "Maybe_ _I'll_ _even_ _let you_ _fuck my mouth again..babe"_ _Leo scoffed and grabbed a shirt to clean them up and afterwards Dean nuzzled_ _into Leo's chest and_ _he passed the fuck out_

~🌈~

_Dean nudged his friends shoulder "Leo wake up" Leo just grunted and stirred a little in his sleep "Leo!"_

_"Ssssh not so loud" He hugged Dean closer not knowing who he was holding and out of curiosity peeked open one eye "Ah!- Dean!" He sat up and clutched the sheets hiding his nakedness "Why are you in my bed?"_

_Dean gave Lee one of his brother's signature bitchfaces and proceeded to lift up the blanket showing Leo his equal nakedness_

_"Fuck" Le_ _o blinked "We had sex didn't we?" He said "Shit, I thought that was just a dream..a really great dream"_

_"Yeah.."_

_Leo smiled "You called me babe" He teased and Dean flushed "That was as a joke" Leo leaned into Dean's space and stared him in the eyes "You sure?"_

_Dean rolled his eyes "Fuck Lee if you're gonna kiss me fucking kiss me" So Leo did, slow at first but it gradually got needier, he dug his fingers in Dean's hair and climed on top of him_

_They both moaned when their dicks touched but both kept kissing enthusiastically_

_Leo ran his hand down Dean's thigh to his calf "God," Leo breathed "You're beautiful"_

_Dean froze "What?-"_

_"I said you're beautiful"_

_Dean shook himself out of it "I've never..no one has ever called me that before" He admitted "-A hot piece of ass yeah- but..only girls get attention..only girls are beautiful"_

_"-Well that's just not true, because you're fucking beautiful"_

~🌈~

"Dean?-Dean?" Sam tried to get Dean's attention, Leo and Sam looked at each other, and Dean shook himself out of the memory "Uh- sorry- what were you saying?"

"I was talking about the case" Sam scoffed with a roll of his eyes "You could at least _pretend_ that you care"

...

"What were you thinking about earlier when you zoned out?" Leo asked when they were now alone in the impala, Dean contemplated lying but he decided against it "..Us"

"What about us?"

"You called me beautiful" Dean said quietly, "After the first time we had sex..you probably don't even remember-"

"-No I remember" Leo insisted, he smiled faintly "You said only girls were beautiful- but I obviously proved you wrong"

Dean sighed "I loved you, y'know?" He said honestly "Every night- _every day_ you made me feel like I was more then just a hunter" Leo nodded "..I loved you too Dean"

"Really?"

Leo scoffed "Of course I did, I just didn't say anything because I didn't wanna ruin everything"

"Huh-..well I can't say that it wouldn't have changed anything" Dean pursed his lips, "There's this guy..Cas- we've been dancing around our feelings for years and I don't know what to do"

"Does he feel the same way?" Leo asked patiently and Dean gave a light nod "Yeah he does- but I'm a fucking coward- everything good in my life I ruin it"

Leo shook his head in protest "No you don't"

"I ruined us" Dean said bluntly "Just like Cassie- and Lisa- and Benny, I can't let Cas be another one of them"

"Dean- it's not your fault you don't ruin everything" Leo said and he wasn't giving Dean the chance to protest "I'll admit letting you go wasn't easy- but you didn't ruin _anything_ "

Dean sighed "..So what's your diagnosis?" Leo faked thought for a second "Come clean, profess your love and run off into the sunset together"

Dean rolled his eyes "Okay now you're pushing it"

~🌈~

They finished the case with thankfully no casualties getting home safe and Leo wished Dean luck on telling Cas

Sam slept through most of the ride a he didn't witness Dean's breakdown about telling Cas and it didn't get any better after they got back

Dean paced in his bedroom, going over Leo's words- he was getting the courage to tell Cas- _well trying_ \- told himself he was ready he had an entire speech prepared

He knocked on Cas' door and when he saw the angel everything he wanted to stay flew out of the fucking window "Hello Dean"

Dean swore there was something stuck in his throat because he literally could not speak, his eyes were found has he stared and Cas in his night sweats and grey t-shirt that complimented his body perfectly

He knew it was a good idea to tell Cas to change his wardrobe, "Dean?- hello?"

"You..you wanna watch a movie with me Cas?" Was what came out and Cas smiled so innocently "Sure" They hadn't had any bestfriend time in awhile

They sat in Dean's room side by side on the bed, they were slowly falling into each others arms cuddling as they watched the tv screen "I don't understand what is so fascinating about a man in a batsuit"

Dean grimaced "Um.. _everything_?" He said like Cas was crazy "He's awesome, not to mention Ben Affleck is super hot"

Cas froze "Oh,"

"What?" Dean prayed to God (which was a bit funny) that Cas wasn't homophobic "You got a problem that I swing both ways?"

Cas didn't really know what that meant but he had an idea "No of course not that's just the first time you've.. _admitted it_ "

Dean felt relief wash over him "Yeah well I figured it's time for a change" He sighed and paused the tv "Hey, I wanna say somethings is that okay?"

Castiel nodded and Dean took a deep ass breath "Cas, you have been with me for years put up with my stubborness and I felt that nothing I could ever give you would be enough" He sighed "I have had a lot people tell me that.. we- _me and you_ are 'mean't to be' and I never believed them..or I just didn't want to"

Cas shifted "Dean..what are you saying-"

"I love you Cas- I love you so much I mean I'd be crazy not to, you're fucking amazing" He cut off "Sorry" He apologized, knowing Cas didn't like it when he swore "See?- I'm even trying to stop swearing for you"

Cas smiled softly "I wanted to give you your time-"

"I don't need anymore angel- I love you and I want the whole fudging world to know it" They stayed silent for a few seconds just staring at each other

It was just..nice, Dean's eyes fell to Cas' _oh so kissable_ lips "..Can I kiss you?"

Cas nodded "Please" _God_ it was everything Dean had ever dreamed of and more, Cas tasted slightly like honey which made Dean want more- Cas dug his hands in Dean dirty blonde hair tugging it as the kiss deepened

Dean slipped his tongue into Cas' mouth and the angel moaned, Dean's hands flew to Cas' waist pushing up his shirt- he didn't really know where he was going with this and he didn't get to find out because the door opened

"Hey Dean- _holy shit_ "

The two jumped away from each other in shock, Dean looked up and wiped his lips with the back of his hand, "Shit Sammy- you ever heard of knocking?" His brother was literally the worst cock block ever

Cas blushed obviously embarrassed, "Um.." Sam didn't say anything, he stared at the two but with a smile "..I'll leave you guys to it then.."

The two silently thanked Sam and resumed their makeout session, everything was going perfectly

Dean's hands slid up Cas' shirt and lifted it over his head, and Cas did the same for him- they kissed some more but before they could got any futher Dean stopped them

"Cas wait"

The angel immediately pulled away and sat up, Dean tried not to stare at his post make out session look and swallowed nervously

Cas frowned "Is everything okay Dean?" God those eyes "..Yeah Cas I just.."

"..You've never been with a man?" Cas assumed, Dean shook his head "No I have, I just..I don't want to rush into this- _us_ we have time" Cas blushed "Oh,"

"..Is that okay?"

Cas nodded "Yes of course, I will gladly wait for you" He seemed sincere "..But we can still cuddle right?"

Dean chuckled "Of course angel"

**Author's Note:**

> PSA
> 
> I was not implying that Dean and Benny had any kind of romantic or sexual relationship- I just meant that Dean felt bad for what happened to him!
> 
> And Happy Bisexual Pride! 🌈


End file.
